Asymmetric Friedel-Crafts alkylation of pyrrole with nitroalkenes catalyzed by a copper complex of a bisphenol A-derived Schiff base

OZDEMIR H. S., Sahin E., ÇAKICI M., KILIÇ H.

TETRAHEDRON, cilt.71, sa.19, ss.2882-2890, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 71 Sayı: 19
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.tet.2015.03.059
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2882-2890
  • Anahtar Kelimeler: Chiral copper complex, Pyrrole, Nitroalkene, Asymmetric Friedel-Crafts alkylation, Asymmetric synthesis, INDOLES, ENONES
  • Atatürk Üniversitesi Adresli: Evet

Özet

The asymmetric Friedel-Crafts (FC) alkylation of pyrrole with nitroalkenes was mediated by CuBr2 and a novel bisphenol A-derived chiral catalyst at room temperature. The catalyst was found to be applicable for the asymmetric FC alkylation of pyrrole with a wide range of nitroalkenes, affording optically active alkylated pyrroles with enantioselectivities up to 94%. Furthermore, enantiomerically pure 3-nitro-2-arylpropanamides were prepared by the oxidative cleavage of the pyrrole rings in the FC products with NaIO4/RuCl3 to demonstrate the synthetic application of the products. (C) 2015 Elsevier Ltd. All rights reserved.